Review
Biochemistry & Molecular Biology
Oszkar Csuvik, Istvan Szatmari
Summary: 8-hydroxyquinoline (oxine) is a well-known and frequently used chelating agent with pharmacological effects that have been studied since the 19th century. The Mannich reaction is a commonly used method to modify its core molecule, which requires mild reaction conditions and simple chemical reagents. This review focuses on the synthesis of aminomethylated 8-hydroxyquinolines via the modified Mannich reaction, utilizing 8-hydroxyquinoline, formaldehyde, and various amines.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Organic
Binyu Wu, Xiaolu Wen, Hongbing Chen, Lin Hu
Summary: A novel formaldehyde, formaldimine, and 1,2-oxazetidine surrogate, N-nosyl-O-bromoethyl hydroxylamine, can serve as a stable reagent under basic conditions to obtain a wide range of synthetically useful compounds via chemo- and stereoselective reactions. Additionally, catalytic asymmetric Mannich reaction of formaldimine equivalent was achieved with moderate enantioselectivities.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Energy & Fuels
Qixiang Kang, Xinghua Zhang, Yanyan Cui, Xuelai Zhao, Wuyu Wang, Jiapeng Zhang, Qi Zhang, Longlong Ma
Summary: Cycloalkanes jet fuel derived from biomass is the perfect alternative to fossil fuel. The Mannich-Michael reaction of cyclopentanone and formaldehyde followed by hydrodeoxygenation (HDO) is a promising method for producing high-density jet fuel. The combination of pyrrolidine and acetic acid showed high catalytic activity in the one-pot Mannich-Michael reaction under mild conditions. By using the enamine catalytic pathway, a high yield of condensed products and conversion of cyclopentanone was achieved. The alkali-treated H beta 25-1 catalyst combined with Pd/C effectively catalyzed the hydrodeoxygenation of the condensed products, resulting in a high yield of dicyclopentylmethane with desirable density and heating value. This work provides a new route for producing high-density jet fuel from lignocellulosic compounds.
Article
Chemistry, Multidisciplinary
Hanwen Yan, Feng Huo, Ping Li, Chunshan Li
Summary: This study presents a detailed mechanistic investigation on the synthesis of methylacrolein (MAL) through a mild Mannich reaction, catalyzed by sec-amine short-chain aliphatic acid ionic liquids (ILs). The catalyst ILs exhibit excellent activity and significantly reduce the reaction energy barrier, resulting in mild reaction conditions. The study provides a thorough explanation of the synthesis mechanism and may have practical applications.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2022)
Article
Chemistry, Organic
Somayeh Darvishy, Heshmatollah Alinezhad, Majid Vafaeezadeh, Sahar Peiman, Behrooz Maleki
Summary: A new approach for the synthesis of ss-amino carbonyl compound has been developed by catalytic Mannich reaction using CSAG at room temperature. This method offers high efficiency, good diastereoselectivity, and catalyst recyclability.
POLYCYCLIC AROMATIC COMPOUNDS
(2022)
Review
Chemistry, Organic
Aslihan Ayvaz, Sinem Gorkem Demirbas, Ahmet Demirbas, Neslihan Demirbas
Summary: Due to the increasing environmental pollution and its detrimental impact on the ecosystem, scientists have developed new chemical strategies using eco-friendly chemicals, solvents, catalysts, and alternative energy sources. Deep eutectic solvents (DESs) are low-melting mixtures primarily consisting of quaternary ammonium salt and hydrogen-bond acceptors. DESs have advantages such as low toxicity, easy preparation, low cost, biodegradability, low vapor pressure, and recyclability.
CURRENT ORGANIC CHEMISTRY
(2023)
Article
Polymer Science
Satyaranjan Behera, Braja N. Patra
Summary: The alum doped nanopolyaniline (NDPANI) is developed as an efficient and reusable green catalyst for synthesis of beta-amino carbonyl compounds through Mannich type reaction. It offers advantages of being inexpensive, reusability, easy preparation, and stability, representing an advanced alternative to established methods with solvent-free condition, mild reaction condition, clean reaction profile, and simple workup.
Review
Chemistry, Organic
Tania Xavier, Sylvie Condon, Christophe Pichon, Erwan Le Gall, Marc Presset
Summary: Substituted malonic acid half-oxyesters (SMAHOs) are an original family of malonic acid derivatives that can serve as pro-nucleophiles for greener methodologies through decarboxylative processes. The presence of a substituent on the malonic position offers opportunities for structural diversification. These reagents are well-suited for the development of organocatalyzed processes, and have recently been used for olefination and addition reactions to synthesize elaborated structures under mild conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Zhihua Cui, Pu Gao, Jinhuan Zheng, Hua Jiang, Weiguo Chen
Summary: This study investigated the selectivity and mechanism of Mannich reaction modification on silk fibroin side groups using dyes containing an aromatic primary amine group. Peptides were designed and synthesized as protein simulations to determine the reaction sites on silk fibroin and describe the reaction selectivity for different amino acid residues. The results revealed that tryptophan and tyrosine residues were the reaction sites for peptide modification, with tryptophan showing stronger reactivity. Additionally, the arginine residue negatively influenced the selective modification of the Mannich reaction. The durable coloration of silk fabrics using aromatic primary amine dyes in the Mannich reaction confirmed the modification of tryptophan and tyrosine residues on silk fibroin, as inferred from the peptide simulations.
Article
Chemistry, Organic
Dau Xuan Duc, Nguyen Thi Chung
Summary: An efficient and environmentally-friendly protocol for synthesizing 2-(arylamino)thiazoles has been investigated. The protocol involves a two-step, three-component reaction using aryl ketones, N-bromosuccinimide, and thiourea derivatives, with [bmim][BF4] ionic liquid as the solvent. The reaction proceeds in a one-pot manner and yields products in good to excellent yields. The ionic liquid can be reused up to five times with minimal decrease in reaction yield. Thirteen thiazoles were synthesized under mild conditions (ambient temperature and short reaction time) with high yields (78-89%), and their structures were confirmed by NMR data.
LETTERS IN ORGANIC CHEMISTRY
(2023)
Article
Polymer Science
Slimane Abdous, Mehdi Derradji, Oussama Mehelli, Raouf Belgacemi, Sarah Soudjrari, Noureddine Ramdani, Karim Khiari, Mohamed El Amine Kadi, Wenbin Liu
Summary: In a study aimed at developing new synthetic routes for energetic materials, two new energetic benzoxazine monomers were synthesized using a two-step Mannich reaction process. The results showed that the benzoxazine monomer based on 2,4-dinitrophenylhydrazine exhibited superior energetic properties. This study demonstrates the potential of using the Mannich reaction to synthesize benzoxazine resins for energetic applications.
HIGH PERFORMANCE POLYMERS
(2022)
Article
Chemistry, Multidisciplinary
Ashmita Mukherjee, Sreyasi Pal, Shivangi Parhi, Sachin Karki, Pravin G. Ingole, Paulomi Ghosh
Summary: In recent years, there has been a global focus on the extraction of bioresources from biowaste using green chemistry for the production of materials, driven by the increasing awareness of sustainability. This study introduces a benign process using an ionic liquid to simultaneously extract keratin and melanin from human hair. The extracted keratin demonstrates hemocompatibility, making it suitable for blood-contacting biomaterials, while the extracted melanin retains its morphology and shows free-radical scavenging activity. The reusable ionic liquid used in the extraction process can potentially be applied in bioelectronics.
Article
Chemistry, Multidisciplinary
A. O. Kurskova, V. V. Dotsenko, K. A. Frolov, N. A. Aksenov, I. Aksenova, B. S. Krivokolysko, S. G. Krivokolysko
Summary: In this study, a series of compounds were synthesized from benzaldehyde, malononitrile, and malononitrile dimer in the presence of excess morpholine, and their structures and biological activities were investigated through experimental and computational methods.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Nipaphorn Ponpao, Warapong Senapak, Rungnapha Saeeng, Jaray Jaratjaroonphong, Uthaiwan Sirion
Summary: This study established a beneficial, scalable, and efficient methodology for synthesizing aniline-based triarylmethanes using a Bronsted acidic ionic liquid as a catalyst, achieving high yields with a broad range of substrates. Additionally, alternative aromatic nucleophiles were also studied, leading to a diversity of triarylmethane derivatives in high to excellent yields.
Article
Green & Sustainable Science & Technology
Kyeongmin Kim, Shinya Nakashita, Kazuki Yoshimura, Tadashi Hibino
Summary: Steel slag as an additional substrate in SMFCs significantly enhances the efficiency of renewable energy production and contributes to the remediation of benthic ecosystem by facilitating the degradation of recalcitrant organic matter and increasing oxidation-reduction potential.
JOURNAL OF CLEANER PRODUCTION
(2021)
Article
Chemistry, Organic
Babak Kaboudin, Samaneh Faghih, Sajedeh Alavi, Mohammad Reza Naimi-jamal, Alireza Fattahi
Summary: This study reports a solvent-free synthesis of 1-aminophosphonates via three-component or two-component reactions, and it is found that no solvent or catalyst is needed for the reactions. Furthermore, a novel method for the synthesis of N-deprotected 1-aminophosphonates is developed.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Physical
Mahya Afkhami-Ardekani, Mohammad Reza Naimi-Jamal, Samira Doaee, Sadegh Rostamnia
Summary: In this study, ZIF-67, a crystalline metal-organic framework (MOF), was synthesized using the solvent-free ball milling method. Platinum metal ions were loaded in the MOF cavities through impregnation. The prepared Pt@ZIF-67 compound was characterized using various methods, and the results showed that Pt nanoparticles were located inside the pores of ZIF-67. Pt@ZIF-67 exhibited high catalytic efficiency in the reduction of nitrophenol compounds in water.
Article
Environmental Sciences
Bahareh Farasati Far, Mohammad Reza Naimi-Jamal, Hossein Daneshgar, Navid Rabiee
Summary: In this study, natural biomaterials and DNA were successfully decorated on ZIF-67 to develop a promising co-delivery platform for the drug DOX-SOR. The modified MOFs showed stable structure and efficient drug loading and release. Cell experiments demonstrated that the decorated nanoparticles not only improved cell viability but also showed anticancer properties.
ENVIRONMENTAL RESEARCH
(2023)
Review
Medicine, Research & Experimental
Bahareh Farasati Far, Kimia Vakili, Mobina Fathi, Shirin Yaghoobpoor, Mohammed Bhia, M. Reza Naimi-Jamal
Summary: MicroRNAs (miRNAs) are small non-coding RNAs that regulate the expression of multiple target genes. They play a significant role in cancer biology by downregulating target genes at both the mRNA and protein levels. miRNAs can be used as cancer biomarkers, and their investigation is crucial for early detection and improved survival rates in gastrointestinal cancers. Specifically, miR-21 is extensively studied in its functions and applications as a diagnostic and prognostic biomarker in colorectal, pancreatic, gastric, and esophageal cancers.
Article
Chemistry, Multidisciplinary
Bahareh Farasati Far, Mohsen Omrani, Mohammad Reza Naimi Jamal, Shahrzad Javanshir
Summary: This study aims to develop two multi-reactive, safe, and highly swellable bio-hydrogels, CS-g-gly and CMCS-g-gly, as potential carriers for sustained and controlled drug release. These hydrogels exhibit high swelling ratios under various conditions and effectively deliver drugs to breast cancer cells.
COMMUNICATIONS CHEMISTRY
(2023)
Article
Multidisciplinary Sciences
Zahra Akhlaghi, Mohammad R. Naimi-Jamal, Leila Panahi, Mohammad G. Dekamin, Bahareh Farasati Far
Summary: 4H-pyrans with ketone and aldehyde groups were synthesized through a mechanochemical multicomponent reaction (MCR) using an amine-functionalized metal-organic framework (MOF) Cu2(NH2-BDC)2(DABCO) as a heterogeneous catalyst, resulting in good to excellent yields.
Article
Chemistry, Applied
Fereshteh Azamifar, M. Reza Naimi-Jamal, Oleg M. Demchuk, Agnieszka Szmagara
Summary: Five series of structurally rigid and worthful pentamethine cyanine dyes were successfully synthesized via a simple and efficient approach. The synthesized dyes exhibited excellent photophysical properties, including bright fluorescence, high molar absorption coefficients, and remarkable fluorescence quantum yield. They also demonstrated outstanding stability and resistance to photodecomposition. The presence of pyridinium substituent rings enhanced the rigidity and water solubility of the dyes.
Article
Polymer Science
Leila Taghi-Akbari, Mohammad Reza Naimi-Jamal, Shervin Ahmadi
Summary: The aim of this research is to improve the fire safety of TPU composites by developing an intumescent flame-retardant (IFR) system consisting of APP, MPP, PER, and nano-silica. The optimal ratio of these flame retardants was determined and TPU/IFR composites were prepared. The cone calorimeter results showed superior fire performance of the TPU/IFR composites, with significant reduction in peak heat release and smoke production rates.
IRANIAN POLYMER JOURNAL
(2023)
Article
Chemistry, Applied
Mojtaba Mirzaei, Sara Hekmat Shoar, Ali Sharifi, M. Saeed Abaee
Summary: The sorption performances of CO2 and N-2 were studied in neat and mesoporous silica supported ionic liquids. The immobilization of ionic liquids onto silica was achieved via wet impregnation-vaporization method. The highest sorption capacities were observed in [C(6)mim][NO3] and (MCM-41)-[C(10)mim][NO3](20). The impregnated solid supported ionic liquids showed a decrease in mesoporosity but an increase in CO2/N-2 selectivity compared to blank solid supports.
JOURNAL OF POROUS MATERIALS
(2023)
Article
Chemistry, Physical
Mojtaba Mirzaei, Ali Sharifi, M. Saeed Abaee
Summary: The solubility of CO2 and CH4 in the ionic liquid 1-benzyl-3-methylimidazolium nitrate ([Bzmim][NO3]) was measured at temperatures ranging from 298.15 to 343.15 K and pressures up to 4.52 MPa for CO2 and 4.22 MPa for CH4. The results showed that CO2 had a significantly higher solubility than CH4 under the experimental conditions. The solubility of CO2 decreased with increasing temperature, while the solubility of CH4 slightly increased.
JOURNAL OF SUPERCRITICAL FLUIDS
(2023)
Article
Materials Science, Multidisciplinary
Morteza Mostashregh, Maryam Khavarpour, Seyed Mohammad Vahdat, Ali Sharifi, Mohammad Ansari, Saghi Sepehri
Summary: This study synthesized a series of novel compounds with biological activities and lower side effects, including 1,4-Benzothiazinone as a new anti-algae product and antibacterial agent to reduce the destructive effects of algae on industrial equipment. Benzothiazinone derivatives were rapidly and environmentally friendly synthesized using the reaction of 2-aminothiophenols and 2-bromoalkanoates, ball milling technique, and solvent-free conditions. The produced compounds showed significant growth inhibition on Spirulina platnesis and excellent activity against Gram-positive bacteria compared to traditional antibiotic (amikacin). In vitro and in silico experiments confirmed the findings.
MATERIALS CHEMISTRY AND PHYSICS
(2023)
Article
Engineering, Multidisciplinary
Bahareh Farasati Far, Mohammad Reza Naimi-Jamal, Sepideh Ahmadi, Navid Rabiee
Summary: Recent advances in osteoimmunology have led to the development of metal-organic framework (MOF)-based porous materials for bone repair. This study focused on the immunomodulatory design of these materials, specifically investigating the effects of Sr2+ and Ca2+ loaded in MOFs on osteogenesis. The results showed that Sr2+ and Ca2+ nanoparticles had a dual effect, promoting matrix secretion by osteoblasts and inhibiting matrix resorption by osteoclasts. HKUST-1@CaNPs/SrNPs showed promising potential for bone tissue engineering.
ALEXANDRIA ENGINEERING JOURNAL
(2023)
Review
Oncology
Bahareh Farasati Far, Maryam Safaei, Fatemeh Mokhtari, Mohammad Sadegh Fallahi, Mohammad Reza Naimi-Jamal
Summary: Current treatment regimens in cancer cases cause significant side effects and cannot effectively eradicate the advanced disease. Proteins as effective medicines for treating progressive diseases like cancer have been under commercial development for over three decades. This review analyzes the potential and limitations of protein therapeutics (PTs) in the treatment of cancer as well as highlighting the evolving strategies by addressing all possible factors, including pharmacology profile and targeted therapy approaches.
Article
Biochemistry & Molecular Biology
Bahareh Farasati Far, Mohammad Reza Naimi-Jamal, Mehdi Jahanbakhshi, Hosein Rostamani, Mahsa Karimi, Shadi Keihankhadiv
Summary: In this study, polycaprolactone-modified chitosan/collagen hydrogel films (CSCPs) were successfully synthesized. Increasing the PCL content improved the tensile properties and hydrophilicity of the hydrogel films, while maintaining good biocompatibility and low hemolysis rates. These characteristics make CSCPs promising candidates for artificial tendon applications.
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
(2023)
Article
Chemistry, Multidisciplinary
Shirin Bondarian, Mohammad G. Dekamin, Ehsan Valiey, M. Reza Naimi-Jamal
Summary: In this study, a cost-effective and convenient method was designed to support Cu(ii) nanoparticles on a modified chitosan backbone. The resulting nanomaterial showed high catalytic efficiency in promoting multicomponent cascade reactions and could be recycled for multiple cycles.
